EP1492834A1 - Polyester amorphe insature a base de dicidolisomeres determines - Google Patents

Polyester amorphe insature a base de dicidolisomeres determines

Info

Publication number
EP1492834A1
EP1492834A1 EP03744708A EP03744708A EP1492834A1 EP 1492834 A1 EP1492834 A1 EP 1492834A1 EP 03744708 A EP03744708 A EP 03744708A EP 03744708 A EP03744708 A EP 03744708A EP 1492834 A1 EP1492834 A1 EP 1492834A1
Authority
EP
European Patent Office
Prior art keywords
acid
unsaturated
amorphous polyester
polyester according
alcohol component
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP03744708A
Other languages
German (de)
English (en)
Inventor
Patrick GLÖCKNER
Alessandro Cerri
Werner Andrejewski
Giselher Franzmann
Peter Denkinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Degussa GmbH filed Critical Degussa GmbH
Publication of EP1492834A1 publication Critical patent/EP1492834A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds

Definitions

  • the invention relates to unsaturated, amorphous polyesters based on certain dicidol isomers and acids.
  • Unsaturated polyester resins are known. They are produced by the condensation of saturated and unsaturated dicarboxylic acids or their anhydrides with diols. Their properties largely depend on the type and quantitative ratio of the starting materials.
  • ⁇ , ⁇ -unsaturated acids are mostly used as carriers of the polymerizable double bonds, primarily maleic acid or its anhydride or fumaric acid; Unsaturated diols are of minor importance.
  • the reactive double bonds in the polyester molecule are therefore “diluted” by condensing in saturated aliphatic or aromatic dicarboxylic acids.
  • Straight-chain and branched diols are used as alcohol components.
  • the individual UP resin types differ not only in the components used for their preparation but also in the quantitative ratio of saturated ones to unsaturated acids, which determines the crosslinking density during the polymerization, the degree of condensation, ie the molecular weight, the acid and OH number, ie the type of end groups in the chain molecules, the monomer content, the type of additives (Ullmann's Encyclopedia of Industrial Chemistry, VOL A21, pp. 217ff, 1992).
  • UP resins based on dicidol as a diol component are e.g. B. known from DE 924 889, DE 953 117, DE 22 45 110, DE 27 21 989, EP 114 208, EP 934 988.
  • the invention relates to unsaturated, amorphous polyesters, essentially containing at least one ⁇ , ⁇ -unsaturated dicarboxylic acid component and an alcohol component, characterized in that the alcohol component consists of a dicidol mixture of the isomeric compounds 3,8-
  • the invention also relates to a process for the production of unsaturated, amorphous polyesters, essentially comprising at least one ⁇ , ⁇ -unsaturated
  • Dicarboxylic acid component and alcohol component characterized in that the alcohol component from a dicidol mixture of the isomeric compounds 3,8-
  • the sum of the three isomers is 90 to 100%, and the mixture is at least 5% present in the alcohol component of the polyester, by reacting the starting components at a temperature of 150 to 270 ° C, preferably in an inert gas atmosphere, the inert gas having an oxygen content of has less than 50 ppm.
  • the unsaturated, amorphous polyester resins according to the invention are obtained by reacting the alcohol component and the acid component.
  • a dicidol mixture of the isomeric compounds 3,8-bis (hydroxymethyl) tricyclo [5.2.1.0 2 ' 6 ] decane, 4,8-bis (hydroxymethyl) tricyclo [5.2.1.0 2,6 ] decane and 5 , 8-bis (hydroxymethyl) tricyclo [5.2.1.0 2 ' 6 ] decane, where each isomer can be present in a proportion of 20 to 40% in the mixture and the sum of the three isomers 90 to 100%, preferably 95 to 100%, and the mixture at least 5% is present in the alcohol component of the polyester.
  • the isomer content of the dicidol mixture can be qualitatively and quantitatively z.
  • the dicidol mixture can contain up to 10% of further isomers of dicidol and / or trimeric and / or higher isomeric diols of the Diels-Alder reaction product from cyclopentadiene.
  • the alcohol component preferably consists of 20%, 50%, preferably 90%, particularly preferably 100% dicidol mixture, this particularly preferably containing 95 to 100% of the above three isomeric compounds.
  • the alcohol component can contain further linear and / or branched, aliphatic and / or cycloaliphatic and / or aromatic diols and / or polyols.
  • Preferred additional alcohols are ethylene glycol, 1,2- and / or 1,3-propanediol, diethylene, dipropylene, triethylene, tetraethylene glycol, 1,2- and / or 1,4-butanediol, 1,3-butylethylpropanediol, 1,3-methylpropanediol, 1,5-pentanediol, cyclohexanedimethanol, glycerol, hexanediol, neopentylglycol, trimethylolethane, trimethylolpropane and / or pentaerythritol are used.
  • the unsaturated, amorphous polyester resins according to the invention contain at least one ⁇ , ⁇ -unsaturated dicarboxylic acid as the starting acid component.
  • the unsaturated polyester resins preferably contain citraconic, fumaric, itaconic, maleic and / or mesaconic acid.
  • phthalic acid isophthalic acid, terephthalic acid, 1, 4-cyclohexanediocarboxylic acid, succinic acid, sebacic acid, methyltetra-, methylhexahydrophthalic acid, hexahydrophthalic acid, tetrahydrophthalic acid, dodecanedioic acid, adipic acid, azelaic acid, or isononanoic acid, 2-ethonanoic acid, isononanoic acid, isononanoic acid, 2-ethanoic acid.
  • Phthalic acid hexahydrophthalic acid, tetrahydrophthalic acid, 1, 4-cyclohexanedicarboxylic acid, adipic and / or azel
  • Some or all of the acid component can consist of anhydrides and / or alkyl esters, preferably methyl esters.
  • the alcohol component is contained in a molar ratio of 0.5 to 2.0 to 1 to the acid component, preferably 0.8 to 1.5 to 1.
  • the alcohol component is particularly preferably reacted in a molar ratio of 1.0 to 1.1 to 1 to the acid component instead.
  • the unsaturated, amorphous polyesters according to the invention can have an acid number between 1 and 200 mg KOH / g, preferably between 1 and 100, particularly preferably between 1 and 50 mg KOH / g and an OH number between 1 and 200 mg KOH / g, preferably between 1 and 100, particularly preferably between 1 and 50 mg KOH / g.
  • the Tg of the unsaturated, amorphous polyester according to the invention varies from - 30 to + 80 ° C, preferably - 20 to + 50 ° C, particularly preferably - 10 to + 40 ° C.
  • the unsaturated polyesters (UP resins) according to the invention consist of an alcohol component with at least 90%, preferably 95%, particularly preferably 100% of the dicidol mixture of the isomeric compounds 3,8-bis (hydroxymethyl) tricyclo [5.2.1.0 2 ' 6 ] decane, 4,8-bis (hydroxymethyl) tricyclo [5.2.1.0 2 ' 6 ] decane and 5,8-bis (hydroxymethyl) tricyclo [5.2.1.0 '] decane and from fumaric acid and / or maleic acid (anhydride ).
  • the polyesters contain the above starting components as under I, but additionally a further acid selected from adipic acid or phthalic acid (anhydride), the ratio of the ⁇ , ⁇ -unsaturated to the additional acid being from 2 to 1 to 1 to 4 can vary. Ratios of approximately 1 to 1 to 1 to 2 are preferred.
  • polyesters generally have acid numbers of 1 to 200 mg KOH / g, preferably 1 -100 mg KOH / g, particularly preferably 1 -50 mg KOH / g, OH numbers from 1 to 200 mg KOH / g, preferably 1-100 mg KOH / g, particularly preferably 1-50 mg KOH / g and a Tg of - 30 to + 80 ° C, preferably - 20 to + 50 ° C, particularly preferred - 10 to + 40 ° C.
  • the polyesters according to the invention can also contain auxiliaries and additives selected from inhibitors, water and / or solvents, neutralizing agents, surface-active substances, oxygen and / or radical scavengers, catalysts, light stabilizers, color brighteners, photosensitizers, thixotropic agents, skin-preventing agents, defoamers, antistatic agents, thickeners, thermoplastic Additives, dyes, pigments, fire protection equipment, internal release agents, fillers and / or blowing agents.
  • auxiliaries and additives selected from inhibitors, water and / or solvents, neutralizing agents, surface-active substances, oxygen and / or radical scavengers, catalysts, light stabilizers, color brighteners, photosensitizers, thixotropic agents, skin-preventing agents, defoamers, antistatic agents, thickeners, thermoplastic Additives, dyes, pigments, fire protection equipment, internal release agents, fillers and / or blowing agents.
  • polyesters according to the invention are produced by (semi) continuous or discontinuous esterification of the starting acids and alcohols in a one-stage or two-stage procedure.
  • the process according to the invention preferably works in an inert gas atmosphere at 150 to 270 ° C, preferably from 160 to 230 ° C, particularly preferably from 160 to 200 ° C.
  • Nitrogen or noble gases, in particular nitrogen, can be used as the inert gas.
  • the inert gas has an oxygen content of less than 50 ppm, in particular less than 20 ppm.
  • Dodecanedioic acid and fumaric acid are reacted with dicidol in a ratio of 1: 1.05 at 180 ° C. in a nitrogen atmosphere until an acid number of 24 mg KOH / g and an OH number of 34 mg KOH / g is reached.
  • the fumaric acid is first esterified with dicidol for one hour and then the adipic acid is added.
  • M n 2200 g / mol
  • M w 5500 g / mol, glass transition temperature 4 ° C.
  • Adipic acid and maleic acid are reacted with dicidol in a ratio of 1: 1.05 at 180 ° C in a nitrogen atmosphere until an acid number of 26 mg KOH / g and an OH number of 37 mg KOH / g is reached ,
  • the maleic acid is first esterified with dicidol for one hour and then the adipic acid is added.
  • M n 1800 g / mol
  • M w 4300 g / mol, glass transition temperature 12 ° C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

L'invention concerne des polyesters amorphes insaturés à base de dicidolisomères déterminés et d'acides dicarboxyliques saturés et/ou insaturés.
EP03744708A 2002-03-21 2003-02-15 Polyester amorphe insature a base de dicidolisomeres determines Withdrawn EP1492834A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10212706 2002-03-21
DE10212706A DE10212706A1 (de) 2002-03-21 2002-03-21 Ungesättigte, amorphe Polyester auf Basis bestimmter Dicidolisomerer
PCT/EP2003/001535 WO2003080703A1 (fr) 2002-03-21 2003-02-15 Polyester amorphe insature a base de dicidolisomeres determines

Publications (1)

Publication Number Publication Date
EP1492834A1 true EP1492834A1 (fr) 2005-01-05

Family

ID=27798034

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03744708A Withdrawn EP1492834A1 (fr) 2002-03-21 2003-02-15 Polyester amorphe insature a base de dicidolisomeres determines

Country Status (16)

Country Link
US (1) US7144975B2 (fr)
EP (1) EP1492834A1 (fr)
JP (1) JP2005527660A (fr)
KR (1) KR20040091149A (fr)
CN (1) CN1643028A (fr)
AU (1) AU2003210284A1 (fr)
BR (1) BR0308572A (fr)
CA (1) CA2472035A1 (fr)
DE (1) DE10212706A1 (fr)
MX (1) MXPA04009041A (fr)
MY (1) MY134367A (fr)
NO (1) NO20044228L (fr)
PL (1) PL370838A1 (fr)
TW (1) TW200305591A (fr)
WO (1) WO2003080703A1 (fr)
ZA (1) ZA200407526B (fr)

Cited By (1)

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DE102007057057A1 (de) 2007-11-27 2009-05-28 Evonik Degussa Gmbh Uretdiongruppen haltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und haftungsverbessernde Harze enthalten

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DE10326893A1 (de) * 2003-06-14 2004-12-30 Degussa Ag Harze auf Basis von Ketonen und Aldehyde mit verbesserten Löslichkeitseigenschaften und geringen Farbzahlen
DE10338561A1 (de) * 2003-08-22 2005-04-14 Degussa Ag Keton-Aldehydharze, insbesondere Cyclohexanon-Formaldehydharze mit geringem Wassergehalt und hoher thermischer Bestätigkeit und Vergilbungsbeständigkeit sowie ein Verfahren zur Herstellung und Verwendung
DE10338562A1 (de) * 2003-08-22 2005-03-17 Degussa Ag Strahlenhärtbare Harze auf Basis von Keton- und/oder Harnstoff-Aldehydharzen und ein Verfahren zu ihrer Herstellung
DE102004005208A1 (de) * 2004-02-03 2005-08-11 Degussa Ag Verwendung strahlenhärtbarer Harze auf Basis hydrierter Keton- und Phenol-Aldehydharze
DE102004020740A1 (de) * 2004-04-27 2005-11-24 Degussa Ag Polymerzusammensetzungen von carbonylhydrierten Keton-Aldehydharzen und Polylsocyanaten in reaktiven Lösemitteln
DE102004031759A1 (de) * 2004-07-01 2006-01-26 Degussa Ag Strahlungshärtbare, haftungsverbessernde Zusammensetzung aus ungesättigten, amorphen Polyestern und Reaktivverdünnern
DE102004039083A1 (de) * 2004-08-12 2006-02-23 Degussa Ag Zinnfreie, hochschmelzende Reaktionsprodukte aus carbonylhydrierten Keton-Aldehydharzen, hydrierten Ketonharzen sowie carbonyl- und kernhydrierten Keton-Aldehydharzen auf Basis von aromatischen Ketonen und Polyisocyanten
DE102004041197A1 (de) * 2004-08-26 2006-03-02 Degussa Ag Strahlungsempfindliche Masse
DE102004049544A1 (de) * 2004-10-12 2006-04-13 Degussa Ag Strahlungshärtbar modifizierte, ungesättigte, amorphe Polyester
DE102004051862A1 (de) * 2004-10-26 2006-04-27 Degussa Ag Dispersionen sulfonsäuregruppenhaltiger, ungesättigter und amorpher Polyester auf Basis bestimmter Dicidolisomerer
DE102004051861A1 (de) * 2004-10-26 2006-04-27 Degussa Ag Verwendung einer wässrigen Dispersion auf Basis eines ungesättigten, amorphen Polyesters auf Basis bestimmter Dicidolisomerer
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DE102005002388A1 (de) * 2005-01-19 2006-07-27 Degussa Ag Wässrige, strahlungshärtbar modifizierte, ungesättigte, amorphe Polyester
DE102005013329A1 (de) * 2005-03-23 2006-11-16 Degussa Ag Niedrigviskose uretdiongruppenhaltige Polyadditionsverbindungen, Verfahren zur Herstellung und Verwendung
DE102005017200A1 (de) 2005-04-13 2006-10-19 Degussa Ag Verwendung eines hochviskosen, weitgehend amorphen Polyolefins zur Herstellung einer Folie
DE102005026765A1 (de) * 2005-06-10 2006-12-14 Degussa Ag Rückenfixierung von Kunstrasenrohware mit Schmelzklebern auf Basis von amorphen Poly-alpha-Olefinen und/oder modifizierten, amorphen Poly-alpha-Olefinen
DE102006000646A1 (de) * 2006-01-03 2007-07-12 Degussa Gmbh Zusammensetzung zur Herstellung von Universalpigmentpräparationen
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DE102006009079A1 (de) * 2006-02-28 2007-08-30 Degussa Gmbh Formaldehydfreie, carbonylhydrierte Keton-Aldehydharze auf Basis Formaldehyd und ein Verfahren zu ihrer Herstellung
DE102007034865A1 (de) 2007-07-24 2009-01-29 Evonik Degussa Gmbh Beschichtungsstoffzusammensetzungen
DE102007034866A1 (de) 2007-07-24 2009-01-29 Evonik Degussa Gmbh Ungesättigte Polyester
US8604105B2 (en) 2010-09-03 2013-12-10 Eastman Chemical Company Flame retardant copolyester compositions
US8758862B2 (en) 2012-06-26 2014-06-24 Prc Desoto International, Inc. Coating compositions with an isocyanate-functional prepolymer derived from a tricyclodecane polyol, methods for their use, and related coated substrates
JP6065645B2 (ja) * 2013-02-27 2017-01-25 三菱化学株式会社 感光性樹脂組成物、これを硬化させてなる硬化物、カラーフィルタ及び液晶表示装置
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DE102007057057A1 (de) 2007-11-27 2009-05-28 Evonik Degussa Gmbh Uretdiongruppen haltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und haftungsverbessernde Harze enthalten

Also Published As

Publication number Publication date
MY134367A (en) 2007-12-31
MXPA04009041A (es) 2005-01-25
JP2005527660A (ja) 2005-09-15
BR0308572A (pt) 2005-01-04
NO20044228L (no) 2004-10-06
WO2003080703A1 (fr) 2003-10-02
AU2003210284A1 (en) 2003-10-08
US7144975B2 (en) 2006-12-05
TW200305591A (en) 2003-11-01
US20050124780A1 (en) 2005-06-09
CN1643028A (zh) 2005-07-20
ZA200407526B (en) 2005-08-29
CA2472035A1 (fr) 2003-10-02
KR20040091149A (ko) 2004-10-27
PL370838A1 (en) 2005-05-30
DE10212706A1 (de) 2003-10-02

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